The 50 Best Rom-Coms of All Time

Since the dawn of cinema, we've been laughing at so many lovestruck hijinks.

By
Rebecca Deczynski

Feb 12, 2016

Art Partner

Since the dawn of cinema, we've been laughing at so many lovestruck hijinks. If you haven't seen these, you're majorly missing out.

1 of 50

When Harry Met Sally (1989)

Can men and women ever truly just be friends? That's the question this film by rom-com queen Nora Ephron attempts to answer. Meg Ryan and Billy Crystal's chemistry is indisputable and, with locations including Central Park in fall, the Metropolitan Museum of Art, and, famously, a table at Katz's Delicatessen, the film also feels like a love letter to New York City.

2 of 50

Funny Face (1957)

Take two of the best actors of the mid-century, throw in some musical numbers and gorgeous Givenchy gowns, and you've got one remarkably lush film. Fred Astaire and Audrey Hepburn are magic on screen and you'll be humming George Gershwin's tunes, like the iconic "S'Wonderful," days after viewing.

3 of 50

Sleepless in Seattle (1993)

The hardships and benefits of long-distance dating ring especially true in this film about a recent widower (Tom Hanks) and a newspaper writer (Meg Ryan) who live on opposite sides of the country. This movie proves that it's possible to find love again, even after total heartbreak, and that daring to follow your instincts will always lead you in the right direction.

This unlikely romance between an unsuccessful bookshop owner (Hugh Grant) and a movie star (Julia Roberts) is a modern fairytale of sorts. Richard Curtis's script also provides an abundance of memorable, touching lines (we all remember Roberts proclaiming, "I'm also just a girl, standing in front of a boy, asking him to love her.") and a lovable group of supporting characters like Grant's onscreen roommate Spike (Rhys Ifans) and zany sister (Emma Chambers).

Charles (Hugh Grant) is always a wedding attendee, never a groom. But his frequent encounters with Carrie (Andie MacDowell) force him to consider the fact that he might have finally met his match. This quirky comedy's wide cast of characters and witty banter from writer Richard Curtis deliver the laughs and make it feel current twenty years on.

The image of Audrey Hepburn clad in a black evening gown in front of Tiffany & Co. is one of the most iconic scenes in movie history, and Hepburn and George Peppard make an enchanting onscreen duo. The film also introduced audiences to Henry Mancini's sweet ballad "Moon River," which went on to win an Academy Award for Best Original Song.

10 of 50

Bringing Up Baby (1938)

Katharine Hepburn and Cary Grant make the unlikely pair of an heiress and a paleontologist, who come together over a mix-up of dinosaur bones and a pet baby leopard. The film was originally considered a flop when it was released, but over time became adored by critics and audiences for its perfect sense of comic timing, pratfalls, and silly situations.

11 of 50

The Princess Bride (1987)

This cult classic centers around the love story of Buttercup (Robin Wright) and Westley (Cary Elwes), fighting pirates, princes, swordsmen, and ROUSs (Rodents of Unusual Size) for the chance to be together. It's also one of the most-quoted rom-coms of all time, with favorites including "As you wish!", "Mawwiage", and "Inconceivable."

12 of 50

Groundhog Day (1993)

Weatherman Phil (Bill Murray) finds himself living Groundhog Day over and over again. But, once he starts falling for Rita (Andie MacDowell), he realizes his seeming immortality can help him win her over as he tries various methods of courting her — and starts improving himself, too. If only real life had a redo button.

Reese Witherspoon is at her Southern best in this rom-com about rising fashion designer Melanie (Witherspoon) who returns home to Alabama to finalize a divorce from her ex Jake (Josh Lucas) before heading to New York City to marry to socialite Andrew (Patrick Dempsey). The film teaches us that sometimes the things we leave behind are what's right for us all along, and it also gave us the line, "You have a baby. In a bar."

15 of 50

Top Hat (1935)

Complications arise when Dale (Ginger Rogers) mistakes Jerry (Fred Astaire) for his producer. But, as the truth unfolds, they only grow fonder of one another. Although Astaire and Rogers made ten movies together, Top Hatis the most playfully romantic of the bunch and, of course, features the flawless dancing the duo is known for.

16 of 50

50 First Dates (2004)

Watching Henry (Adam Sandler) attempt to form a normal relationship with Lucy (Drew Barrymore) in spite of her short-term memory loss is wholly entertaining, sweet, and perfectly zany. Filmed in Oahu, this flick also scores romance points for its stunning Hawaiian scenery.

17 of 50

My Best Friend's Wedding (1997)

It's impossible not to sympathize with food critic Julianne (Julia Roberts) when she realizes she's in love with her best friend Michael (Dermot Mulroney) only after he gets engaged to perky young Kimberly (Cameron Diaz). The moments between Julianne and her editor George (Rupert Everett) make for the biggest laughs, and who can forget the group sing-along scene to Dionne Warwick's "I Say a Little Prayer?"

18 of 50

The Wedding Singer (1998)

Wedding singer Robbie (Adam Sandler) and waitress Julia (Drew Barrymore) may work together, but somehow, they're both engaged to the wrong people (Julia Guglia!). The music, pop-culture references, and outrageous fashion of the 1980s makes this rom-com even funnier, as do several musical performances by Sandler, including our favorite: "Love Stinks".

19 of 50

You've Got Mail (1998)

This late '90s flick may be an early example of falling in love over the Internet, but its message still rings true in today's tech-driven world: sometimes the best thing for your love life can be the World Wide Web. Tom Hanks and Meg Ryan have starred in three films together, but You've Got Mail is our pick for the one that best showcases their onscreen chemistry.

20 of 50

About A Boy (2002)

It's true: sometimes kids know best. It takes 12-year-old Marcus (a young Nicholas Hoult) to show Will Freeman (Hugh Grant) what love and relationships are all about. This is a rom-com about growing up—for grownups.

21 of 50

The Proposal (2009)

Margaret (Sandra Bullock) insists that her employee Andrew (Ryan Reynolds) marry her so she can avoid deportation to Canada. But, as they head to Alaska to meet his family, both begin to realize they may actually attracted to one another. Andrew's dreamy family home is worth watching the film for alone, and we also love Betty White's turn as Andrew's lovable, albeit raunchy, grandma.

22 of 50

Clueless (1995)

As if! Based on Jane Austen's Emma, this Valley Girl classic starring Alicia Silverstone is a not only about unexpected love, but also about how relationships evolve with your best girlfriends, too. The majorly quotable script and over-the-top 90s fashions are totally a plus.

23 of 50

Roman Holiday (1953)

Audrey Hepburn stars as bored Princess Ann, who escapes from her guardians for an adventure with American newsman Joe Bradley (Gregory Peck). The streets of Rome serve as the backdrop for their blossoming relationship and, thanks to the movie's iconic scooter scene, driving a Vespa around city streets with your crush is now on every romantic traveler's to-do list.

It seems like Peter (Jason Segel) can't catch a break when he runs into his ex Sarah Marshall (Kristen Bell) in Hawaii, but this comedy of errors shows that somehow, things always end up the way they're meant to be.

26 of 50

Coming to America (1988)

Prince Akeem (Eddie Murphy) abandons tradition when he leaves his fictional home country to search for the love of his life in Queens, New York instead of opting for an arranged marriage. Antics ensue, but with the help of his sidekick Semmi (Arsenio Hall), Murphy eventually finds his match.

27 of 50

Amélie (2001)

This whimsical French film centers around an innocent girl (Audrey Tautou), who decides to help those around her and who ends up falling in love with a stranger along the way. It's a feel-good flick that encourages chasing love, even if it's hard to fully track down.

If you were a teen the 80s, you likely coveted the wardrobe of Andie (Molly Ringwald), a girl from the poor side of town who falls for pretty rich boy Blane (Andrew McCarthy). While many argue Andie should fall for her sweet friend Duckie (Jon Cryer) instead, Pretty in Pink reminds us that you can't choose who you love, and that forgiveness and acceptance are essential.

30 of 50

His Girl Friday (1940)

Career and romance go hand-in-hand in this comedy. When a star newspaper reporter (Rosalind Russell) tries to quit her job before re-marrying, her editor/ex-husband (Cary Grant) offers her a lead on a major story in an attempt to keep her.

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